Textile assistants and process for preparing the same



Patented Aug. 24, 1937 'rnx'rrm assrs'ran'rs AND raoos'ss roa PREPARING'rnx ssm:

Henry Alfred Piggott, Cheadle Hulme, England, or to Imperial-ChemicalIndustries Limlted, a corporation of Great Britain No Drawing.Application February 8, 1934, Se-

PATEN -or 2,091,105 FlCE rial No. 710,387.

' 16 Claims.

This invention relates to chemical compounds which are valuable textileassistants, and a procass for the manufacture thereof.

It is an object of the present invention to produce new chemicalcompounds. A further oblast is to produce new chemical compounds whichare valuable detergent agents. A still further object is the productionof new chemical compounds whlch are valuable dispersing agents,

[0 wetting-out agents, emulsifying agents, softening agents orvat-retarding agents. Other objects will appear hereinafter. v

These objects are accomplished by producing chemical compositions by theprocess which comprises interacting with an alkylene oxide an amine ofthe following general formula,

' wherein R1 is a straight-chain higher aliphati radical, that is, onehaving at least 8 carbon atoms, Y stands for CH: or 00, x stands forhydrogen or a lower alkyl, while R: is the radical of apolyhydroxy-alkyl compound containing at least two OH groups. Thechemical compositions obtained or obtainable in this way may beconverted to further new chemical compositions by treating them with asubstance chosen from the group which comprises alkylating agents and 0esterlfying agents to effect partial alkylation or esteriflcation of thefree OH groups. A preferred alkylene oxide is ethylene oxide. Preferredamines are water soluble ones. The interaction of the amine and alkyleneoxide may be eilected by heating, which may be without a catalyst andeven without a diluting medium, heating being eifected when necessary ina closed vessel. The amine may if desired be used in the form of a salt.When an acylamine is chosen as startin 40 material this shouldpreferably be a carboxylamide or a sulphonamide.

While the invention is susceptible of considerable variation andmodification in the manner-of its practical application, particularly asregards the specific materials used, the proportion thereof and themethod of their preparation, the fol- V lowing examples, in which theparts are by weight,

will serve to illustrate some of the products falling within theinvention and how they may be prepared.

Example 1.--A mixture of 150 parts of N-stearyl-p, p, p"-trihydroxy-tert.-butylamlne with 90 parts of ethylene oxide (5.3molecular equivalents) is heated in a closed vessel by raising thetemperature to 120 C. uniformly during 5 hours, and then keeping at thistemperature until the internal pressure falls to zero. The product is aviscid yellow gum which dissolves readily in water to a colourless,faintly .alkaline solution.

59 Addition of this product to an indigo vat lowers In Great BritainFebruary the rate of dyeing of material immersed in the vat, andmarkedly improved the fastness to rubblng of the finished dyeing.

N-stearyl-p, p, p"-trlhydroxy-tert.-butylamine may be prepared byheating together 5. B, B trihydroxy-tert.-butylamine (cf. Piloty andBud, Ben, 1897, 30, 1665, 2072) and stearlc acid as described in mycopending application Ser. No. 715,776, now Patent No. 1,985,424 issuedDecember 25, 1934.

Example 2.-50 parts of N-cetyl-p, p, p"-trihydroxy-tert.-butylamlnehydrobromide and 50 parts of ethylene oxide (9.7 molecular equivalents)are heated togetherunder the conditions of the previous example. A brownsemi-solid body is produced, readily soluble in water to a paleyellowsolution.

bL-cetyl-p, p, p"-trihydroxy-tert.-butylamine hydrobromide may beprepared by heating 3, p, p"-trihydroxy-tert.-butylamine with cetylbromide at 160 0., and separating from the dicetyl derivativesimultaneously formed by dissolving in methyl alcohol and filtering.

Example 3.Methylcetylglucamine (60 parts) and ethylene oxide (60 parts)are heated together under the same conditions as in Example 1. Theproduct is a dark brown semi-solid mass, readily soluble in water to analkaline solution. It is a valuable dispersing and emulsifying agent.

Methylcetylglucamine is prepared by reacting together methylamine andglucose in the presence of nickel and hydrogen at -100/1000 lbs. per sq.in., and combining the resulting methylglucamine with cetyl bromide.

Example 4.--'I'he product from Example 3 is heated with one third of itsweight of the chloride of stearic acid and one sixth of its weight ofpyridine at C. for k hour and cooled. The resulting solid product is awhite, waxy substance, which dissolves in water to a strongly foamingsolution.

Example 5.l25 parts of the product of Example 3 are heated with 57 partsof stearic acid. the temperature being gradually raised from -160 C.over a period of 6 hours. By the end of this time a completelywater-soluble product is formed.

Example 6.A mixture of 22 parts of B, 'v-dihydroxy-n-propylamine and 66parts of stearic acid is stirred at 100 C. until combination to awater-soluble soap has occurred. This-is then heated at C. until wateris no longer evolved and the product is completely soluble in benzene.0n cooling a white waxy solid, soluble in hot water to-a solution whichsets to a gel on cooling is obtained. 80 parts of this product areheated with 60 parts of ethylene oxide in a closed vessel until theinternal pressure falls to zero. A white solid of somewhat lower meltingpoint is thus obtained. It is readily soluble in cold water to a froclear solution and has powerful emulsifying and dispersing properties.When added to an indigo vat it causes a slight brightening in the shadeof the dyed fabric and markedly improves its festness to rubbing.

As many apparently widely difierent emhodi= ments of this invention maybe made without de-= parting from the spirit and scope thereof, it is tobe understood that we-do not limit ourselves to the specific embodimentsthereof except as de= fined in the following claims.

wherein R; is a straight-chem higher aliphatic v radical, Y is a memberof the group consisting of CH2, and 00, X is a member oi the groupconsis'ting oi hydrogen and the lower allryls, while It: is the radicalof a polyhydroxy-allryl comocund containing at least two OH groups.

2. process as in claim 1, wherein the amine is employed in the i'orm ofa hydroholide.

3. A process in claim 1, the proportion of allsylene oxide to the amineemployed losing not less than 5 mole of the former to 1 moi. of thelatter, 7

t. A process for producing textile assistants, which comprises reactingwith an allryiene oxide upon e lens-chain aliphatic nitrogenous organicconinouno. of the general formula Ri-Y'1? 'R2 wherein R1 is astraight-chain higher aliphatic radical, it stands for a member of thegroup consisting of CH2 end C0, X stands for a member of theuroup'consisting of hydrogen and the lower sllrylis, while'Rz is theradical oi a polyhydrony=alhyl compound containing at least two OHgroups, and partially esterifying the inter meoliete reection productthus obtained,

5. The process of producing a textile ussist= ant which comprisesheating together in a closed vessel from about 5 to about lil molarpropor= tions of ethylene oxide and about ll molar pro portion of acompountl oi the general formula wherein R1 is a higher aliphaticradical having from 15 to 17 carbon atoms, X stands ior a mern-= her ofthe group consisting oi hydrogen sud methyl, and R2 stands for apolymdroxs almi ensures radical having not more than 6 carbon atoms andnot less than two H groups.

6. the process of producing a textile assistant which comprises heatingtogether in a closed vessel from about to about molar proportions ofethylene oxide and about 1 molar proportion of a compound of the generalformula wherein R1 is a higher aliphatic radical having from to l?carbon atoms, K stands for a member of the group consisting of hydrogenand methyl, and R2 stands for a-polyhydroiw-alwi radios-t1 having notmore than 8 carbon atoms and not less than two OH groups, and thenheating the reaction product with from one-third to about one-half ofits-own weight oi a higher aliphatic-acid esteriiyins agent to efiectpartial esteriiication.

l. The process which comprises heating N- stearvl ,8, p, e" trihydroxytertiary hutyl amine with not less than about 5 molecular equivalents ofethylene oxide, in a closed vessel at shout 120 C. until the increasedpressure within the vessel has substantially suhslueol, end recoveringthe reaction product.

s. The compounds obtainable Test the defined in claim 1.

9. The compounds obtainable by the defined in claim e.

to. The compounds obtainable he the process defined in claim 5.

ii. The compounds obtainable hy the deflneol in claim 6.

22. The compounds obtainable hr the defined in claim T.

13. A compound oi the series ohtainnhie re= noting ethylene oxide with scompound oi the general formula process process wherein R1 represents ahigher elhyi radical, ll; stands for a member of the group consisting ofhydrogen and methyl, and R3 stands for e, poly hydroxy lower allrylradical containing at least two 0H groups.

it. The partial esteriiication product of :2; compound as defined inclaim is with a higher eliphatic acid.

is, The condensation product of N-stearyi= it, e, B trihvdrony tertieryhutclamine with about 5 mole of ethylene crude.

it. The condensation product of N-cetyl 3, ii, 3 trihydroxy tertiaryloutylumine hu urobromiue with about 10 mole of ethylene oxide.

HENRY memos: PIGGUH.

